75561-13-6

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 64-19-7 acetic acid 
• 931-17-9 1,2-Cyclohexanediol 
• 1792-81-0 cis-1,2-cyclohexane 
• 286-20-4 cyclohexene oxide 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 110-83-8 cyclohexene 

Downstream Products

• 170749-13-0 2-nitroxycyclohexyl acetoacetate 
• 170749-06-1 2-nitroxycyclohexyl cyanoacetate 
• 170748-93-3 2-nitroxycyclohexyl 2-(3-nitrobenzylidene)acetoacetate 
• 1027981-90-3 Isopropoxycarbonimidoyl-acetic acid 2-nitrooxy-cyclohexyl ester 
• 175416-74-7 (+)-trans-1-acetoxy-2-nitroxycyclohexane 

Relevant academic research and scientific papers

Kinetics and products of the reactions of OH radicals with cyclohexene, 1-methyl-1-cyclohexene, cis -cyclooctene, and cis -cyclodecene

Rate constants for the reactions of OH radicals with four C 6-C10 cycloalkenes have been measured at 297 ± 2 K using a relative rate technique. The rate constants (in units of 10 -11 cm3 molecule-1 s-1) were cyclohexene, 6.35 ± 0.12; cis-cyclooctene, 5.16 ± 0.15; cis-cyclodecene, 4.18 ± 0.06; and 1-methyl-1-cyclohexene, 9.81 ± 0.18, where the indicated errors are two least-squares standard deviations and do not include uncertainties in the rate constant for the reference compound 1,3,5-trimethylbenzene. In addition, a rate constant of (4.8 ± 1.3) × 10-11 cm3 molecule-1 s-1 was derived for the reaction of OH radicals with 1,6-hexanedial, relative to our measured rate constant for OH + cyclohexene. Analyses of products of the OH + cyclohexene, 1-methyl-1-cyclohexene, and cis-cyclooctene reactions by direct air sampling atmospheric pressure ionization mass spectrometry and/or by combined gas chromatography-mass spectrometry showed the presence of products attributed to cyclic 1,2-hydroxynitrates and the dicarbonyls 1,6-hexanedial, 6-oxo-heptanal, and 1,8-octanedial, respectively. These dicarbonyl products, which are those formed after decomposition of the intermediate cyclic 1,2-hydroxyalkoxy radicals, were quantified as their dioximes, with molar formation yields of 76 ± 10%, 82 ± 12%, and 84 ± 18% from the cyclohexene, 1-methyl-1-cyclohexene, and cis-cyclooctene reactions, respectively. Combined with literature data concerning 1,2-hydroxynitrate formation from OH + alkenes and the estimated fractions of the overall reactions proceeding by H-atom abstraction, 90 ± 12%, 95 ± 13% and 108 ± 20% of the products or reaction pathways from the OH radical-initiated reactions of cyclohexene, 1-methyl-1-cyclohexene, and cis-cyclooctene in the presence of NO are accounted for.

1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate: An efficient reagent for synthesis of Β-nitrato alcohols

A simple and efficient method for the ring opening of epoxides to-hydroxy nitrates has been achieved in the presence of ammonium nitrate and 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate.

In vitro inhibition of human erythrocyte glutathione reductase by some new organic nitrates

Glutathione reductase (GR), is responsible for the existence of GSH molecule, a crucial antioxidant against oxidative stress reagents. The antimalarial activities of some redox active compounds are attributed to their inhibition of antioxidant flavoenzyme

Tetranitromethane as an efficient reagent for the conversion of epoxides into β-hydroxy nitrates

A convenient regioselective method for the preparation of β-hydroxy nitrates based on the ring opening reaction of epoxides by tetranitromethane in the presence of triethylamine is described. A series of substituted β-hydroxy nitrates were obtained in high yields under mild conditions.

Efficient regio- and stereoselective conversions of oxiranes and aziridines into β-(nitrooxy)-substituted alcohols and amines by using bismuth nitrate

Oxiranes and aziridines efficiently undergo ring opening with bismuth nitrate at room temperature to furnish the corresponding β-(nitrooxy)- substituted alcohols and amines respectively. The conversions are highly regio- and stereoselective and afford the

Zirconyl nitrate mediated regioselective ring opening of epoxides and aziridines: an easy synthesis of β-nitrato-alcohols and -sulfonamides

Epoxides and aziridines are cleaved efficiently and regioselectively in the presence of zirconyl nitrate at room temperature to afford the corresponding β-nitrato-alcohols and -sulfonamides, respectively, in high yields.

Regio- and diastereoselective ring-opening reaction of epoxides with nitric oxide

Ring-opening reactions of epoxides with nitric oxide afforded syn or anti α-hydroxy nitrates in high regio- and diastereoselectivities in good yields. Copyright Taylor & Francis Group, LLC.

Micellar media for the efficient ring opening of epoxides with CN-, N3-, NO3-, NO2-, SCN-, Cl- and Br- catalyzed with Ce(OTf)4

Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN, N3-, NO3-, NO2, SCN, Br and Cl-, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN- is an easy procedure for the high yielding preparation of epoxy sulfides.

Iron(III) trifluoroacetate as an efficient catalyst for solvolytic and nonsolvolytic nucleophilic ring opening of epoxides

Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.

Bu3SnH-Mediated Pinacol Coupling of 1,5- and 1,6-Dicarbonyl Compounds: Synthetic and Mechanistic Studies

A new method is described for the intramolecular pinacol coupling of 1,5- and 1,6-dicarbonyl compounds, employing Bu3SnH as the stoichiometric reductant. The key steps in this pinacol cyclization are the addition of a tin ketyl to a carbonyl group and a subsequent intramolecular SH2 reaction. The isolation of 1,3-dioxa-2-stannolanes, along with other product and labeling studies, provides strong support for the proposed homolytic substitution step, which distinguishes the pinacol cyclization from other reductive cyclizations of tin ketyls, all of which proceed through abstraction of hydrogen from Bu3SnH in the final step. An interesting consequence of the SH2 pathway is very high cis selectivity in the cyclization of 1,5-dicarbonyl compounds. Mechanistic studies furnish evidence that the steps that precede homolytic substitution, including C-C bond formation, are reversible under the reaction conditions.